Winner Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Nov 28 - Nov 30
In two months
Jan 9 - Jan 11
In three months
Feb 6 - Feb 8
In four months
Mar 6 - Mar 8

Vacation Rentals in Winner

Exterior
Cozy Little Getaway, Winner, SD

Cozy Little Getaway, Winner, SD

Winner
10.0 out of 10, Exceptional, (10)
"We enjoyed our stay—there was Netflix on all the TVs and plenty of beds. "
United States
Mike T.
$150 nightly
The price is $154
Dec 1 - Dec 2
Total with taxes and fees
Cozy Little Getaway, Winner, SD
Dining
Rustic Ridge

Rustic Ridge

Gregory
9.6 out of 10, Exceptional, (4)
"The house is very clean & well kept, everything we needed was supplied. It's very easy to get to; private & quiet."
United States
Lynn D.
$326 nightly
The price is $342
Nov 15 - Nov 16
Total with taxes and fees
Rustic Ridge
Microwave, oven, stovetop, dishwasher
Centrally located spacious house in Valentine, 4 bedrooms, 5 beds, sleeps 8

Centrally located spacious house in Valentine, 4 bedrooms, 5 beds, sleeps 8

Valentine
8.0 out of 10, Very Good, (2)
"Central location is a plus. Restaurants good. Home is comfortable and Cindy is very easy to work with."
United States
Jeffrey B.
Centrally located spacious house in Valentine, 4 bedrooms, 5 beds, sleeps 8
Exterior
Valentine’s Tourist Tenure- Charming 2 bedroom cozy vacation home

Valentine’s Tourist Tenure- Charming 2 bedroom cozy vacation home

Valentine
10.0 out of 10, Exceptional, (3)
"Cozy place! Walking distance to many things."
United States
Janet W.
Valentine’s Tourist Tenure- Charming 2 bedroom cozy vacation home
Exterior
The Ranch You Love

The Ranch You Love

Dallas
9.6 out of 10, Exceptional, (17)
"The area was very quiet and remote. Recommend if looking to get off the grid of daily life"
United States
Jennifer P.
$440 nightly
The price is $462
Nov 16 - Nov 17
Total with taxes and fees
The Ranch You Love
Microwave, oven, stovetop, dishwasher
Sandhills retreat minutes from downtown Valentine

Sandhills retreat minutes from downtown Valentine

2.0 star property
Valentine
Sandhills retreat minutes from downtown Valentine
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winner Hotel Reviews

Harmony Inn & Suites

Harmony Inn & Suites

10/10 Excellent
"All good "
Randy 1-night trip
Posted 6 days ago
Harmony Inn & Suites

Find out more about Winner

Everything you need to know about Winner vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winner vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winner vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winner vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winner. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winner in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $154 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winner rentals

At Expedia, we put the best Winner vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winner rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winner vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winner. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Winner?

Yes, there are vacation rentals near top local attractions in Winner, or you can select a more remote option if you're looking for relaxation. Winner is known for its golf courses and churches. Make sure you have time to check out the monuments while you're in the area.

What are some of the best vacation rentals in Winner?

Cozy Little Getaway, Winner, SD: Visitors like this Winner vacation home rental. It has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

What can I see and do in Winner?

Take time out to visit local sights such as Winner City Pool, Winner Country Club, and Tripp County Veteran’s Memorial. In the larger area, you’ll also find Beaulieu Lake.

What are vacation rentals like in Winner?

Vacation rentals are privately owned properties you can book for several days or longer in Winner. Vacation rentals provide amenities such as patios, hot tubs, and fire pits to help you enjoy your stay. If you're concerned about a clean environment, a vacation rental can provide a sense of privacy away from shared hotel elevators and busy lobbies while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental a popular choice for families.